Many of my childhood summer family vacations consisted of too-long family truckster car trips to unglamorous destinations where my father had secured a consulting project. He worked on cable TV systems, the “head-ends” for which are usually on the outskirts of sleepy towns where, I am confident, most Americans do not vacation. Utica, NY. Gadsden, AL. Charleston, WV. Houma, LA. Midland, MI. I’m sure these are perfectly nice places to live – but once you’ve seen one Days Inn motel room, you’ve kind of seen them all.

Usually my father drove and my mother sat in the passenger seat. We’d load most of the suitcases into the middle of the station wagon, and then my brother and I would inhabit the “way back”. Sometimes we would climb over the piled suitcases in the mid-section and get horizontal as we cruised down I-95.

This was in the days before iPads and built-in DVDs, so on our drives from home in Lawrenceville, NJ to Commerce, GA (our frequent first stop when heading south), we had to amuse one another. When we got thirsty, we’d ask my mother for a cup of iced tea; she’d dispense a cup from the cooler that she’d filled that morning with an ample supply of Shop Rite’s own brand of powdered, sweetened iced tea.

This image came to my mind in a flash the other day when I found myself behind the wheel on the New Jersey Turnpike, Nova to my right, the kids in the back seat, on our first-ever road trip as a family. We are in the Outer Banks, so it’s not quite Meridian, MS, where I did once spend a few days at what I think was a Rodeway Inn. But it was eerie just the same. The familiar buzz of the highway flying past, the blinking white lines in the middle of the road, the faded Stuckey’s billboards and constant lookout for radar trips all only added to the sensation.

About 300 miles later, we crossed the Chespeake Bay Bridge tunnel. It’s a long stretch through Virginia and then out of nowhere, you are flying across the Chesapeake. My kids had the same experience I did the last time we crossed it as a family almost 40 years ago: sheer boredom followed by 20 minutes of wonder. My father was driving, of course. It is strange to think of him as so in command, which back then was all I knew of him. A confident man in command.

My kids certainly have the sensation in front of them as well of discovering how fragile their father really is

As a circle of life moment, that flash on the New Jersey Turnpike is a minor one in the life of a Sandwich Generation father. The sweet tea memory is a mundane one, in some ways. But then I suppose that those are the ones that sneak up, and stay with you.

When I used to buy condoms 700 years ago, I was careful to do two things. First, in a case of “optimism kills”, I stopped buying big boxes. Inevitably they led to breakups or droughts. Second, I always bought bubble gum with them. In my earliest days of buying them, I was nervous so this made me feel less conspicuous. Yes this was ridiculous but remember, it was 700 years ago. Then it just became a habit.

This popped into my head the other day at CVS when I was browsing adult diapers and pads. As a Sandwich Generation dad, I am many years removed from buying either condoms for myself or diapers for my now 12 year-olds. (Note: for them, puberty is the more imminent and scary challenge). Incontinence, however, is becoming a bigger problem for the other half of the sandwich. Hence my reading labels and trying to figure out a solution. There are many reasons that the standard adult protective underwear, if you will, will not work for my dad.

That’s a whole other post. What I will say is that when it comes to compromising purchases, I find that I still prefer to make them alongside gum. Some things never change.

I used to be an adjunct professor in the MBA program at Babson and lecture on entrepreneurship. One of my most popular anecdotes was something I entitled with only minimal exaggeration “My Mother Isn’t So Proud of Me Anymore.” It is a tale of ever-descending brand equity of my employers, from Morgan Stanley, to Wells Fargo, to Exodus (who?), to working for myself, and sliding on down to owning a share of a Five Guys burger franchise. My mother used to measure vacations by the quality of the motel (eventually hotel) rooms in which we stayed and how low she could crank the air conditioning. So, for her, my devoting time, money and energy to serving better French fries to a medium-sized county in Massachusetts was something less than a dream come true.

“You didn’t go to Duke and Stanford so that you could work in a hamburger restaurant,” she told me.

“Well, I’m an owner, that’s different,” I tried to explain.

She paused to consider this, trying to absorb that each person in line was about to make a very small contribution to our income. Then she asked me a question.

“But isn’t your office actually in the back of the restaurant?”

“Sure.”

“So,” she pointed out, “you do work in a hamburger restaurant.”

I bring this up in a blog nominally about being a Sandwich Generation father because the balance of career and family is something that I have burned a lot of energy thinking about. It’s a new phenomenon that men even think about this; even millenials are considering it, although I’m sure in a “of course I can have it all” kind of way. More relevant to me is someone like Max Schireson, who was CEO of a tech company and quit because he felt he couldn’t do that and be a good father; his story is outlined in this great article in the New Republic.

Now that I am between full-time roles, I am considering this anew before I just jump into another extremely demanding executive role in a fast-growing business. My past job had so much about it I loved, but keeping things balanced was a high-wire act (see: The Juggling) that I am sure at times got the best of me. There are two main questions I am starting to really think about.

First, what does “career” even mean?

My father sometimes introduces me as “the ex-millionaire”. For a brief blip in time, my stock in my employer (Exodus – I know, “who?”) was worth over $6 million on paper. I still remember him calling me at work solely to inform me of that. Even then I knew that it would not last; before long, the Internet bubble burst and we were done in by too few customers and too much debt. Exodus actually went bankrupt twice, which is a pretty amazing accomplishment.

Anyway, I did not cash in millions. Part of me wonders whether my father somehow enjoys that fact, as his professional path was completely different.

For decades, he made a living as a one-man consultant in the Cable TV industry. He would pile complex signal testing instrumentation into his faux wood paneled station wagon and drive hundreds or thousands of miles to television reception towers on the outskirts of small towns in Alabama or West Virginia or Michigan. Once he had a project in Guam. Then he would drive back home and with my mother’s help, quickly compile a lengthy report and FedEx it.

His worn and oversized office desk and chair now sit in his apartment; my brother and I couldn’t bear to move him without them. They define him.

If we are the products of our parents, I have these two people on either shoulder. Sandwiched between them, if you will. One is saying “get a nice safe job at a big company that puts you up in nice hotels”. The other is saying “screw it, you don’t need anybody, just be a one-man consultant.” They can’t both be right.

Then, there is the question of what “balance” means.

In the midst of that parental cacophony, I hear two other voices. The first voice, which sounds a lot like my own, says, “you should have achieved more by now. You’re 45 years old! Time is running out!” And then another voice, which sounds suspiciously like Nova’s, chimes in with “What are you talking about? Focus on what actually matters to you and make work fit into that.”

In other words, you cannot have it all. You cannot drive yourself to accept nothing less than complete devotion to company or career, and simultaneously be present for your family and your community. You have to choose. Specifically, I have to choose.

A few weeks ago, I got another surprising data point for this internal debate. I was helping my father do some math around his finances. The arithmetic was pretty shocking as it says that he is likely to outlive his money. This was a real jolt for him. He always has worried about money; he was raised in the Depression in Hungary after all. He and my mother had epic screaming matches about the quality of the roadside motels we’d spend our summer vacations in. That’s an argument he was going to win either way, if you get my meaning.

But this time, he paused briefly, and in a quieter tone than usual, he noted the irony of having money and suddenly not being able to go anywhere, do anything, or otherwise use it. I could almost see him cataloging the things my mother asked for that he’d said no to, that maybe he wished he hadn’t. Somewhere deep in his mind I think he was apologizing to her.

To me, he was saying that I should invest more time, and therefore more money, to make a thoughtful decision.

So I am lucky enough right now to have a first-world ex-millionaire situation: looking for my next venture or job that balances “career”, whatever that actually means beyond quieting restless Type A self-doubt, with my more meaningful obligations as a husband and a Sandwich Generation dad with 12 year-olds who still love me and a 91 year-old father who is still razor sharp. The clock is ticking on both of those, I know.

Maybe I could tweak my mother one last time beyond the grave by ditching the whole thing and becoming a full-time self-employed blogger. Stranger things have happened.

As Sandwich Generation dad, I serve many functions for my own father. Primary medication distributor. Friend and companion. Personal shopper. Dedicated email correspondent – he sends a lot of email, much of it about recently about why Fox News is right. (I try to tell him that Megyn Kelly being attractive doesn’t mean that the network is always right, but I’m losing that battle.) Pedicurist (not my favorite role). Main technical support guy – only yesterday I bought him a new iPad and Zagg keyboard as his old ones are grinding to a halt.

Among these, one of the most demanding and complex is being his CFO: bookkeeper, investment advisor, compliance officer, head lawyer, and insurance manager. In particular, I manage his money. This was not a straight path from Point A to Point B. In thinking about it, I realized that like grief, it meandered at its own pace through the same 4 stages: denial, anger, depression, acceptance.

Denial

In this phase, the adult parent pretends there is no problem. My mother had managed the finances (along with most everything else) in the house, so after she passed away, my father was confronted with how to keep the bills paid. Or, rather, my brother and I were confronted with it as he had just enough interest in the problem to let us solve it for him. Which we did by (a) automating everything in sight, (b) consolidating the almost 10 bank accounts into one, and (c) trying to fix a very confusing credit card situation. We also got passwords to everything – which if you haven’t done with your parent already, you should do now BEFORE you really need to. Trust me.

We also pulled his investments from the full-service broker who, based on the floor-to-ceiling envelopes stuffed with trade confirmations suggested, somehow had turned my mother into a day-trader. We moved them instead into nice, simple, boring index funds at Fidelity.

Anger

Next the parent says “I can do this myself – what the hell do I need these kids for?” For us this happened about 4 or 5 months later. He changes the online banking password so that you are locked out, pays his own bills for a while, and to prove that he is smarter than you, moves all the money to a full-service brokerage at the bank down the street. Then he tells you “what the hell did I need you for anyway?” Then he brags to your wife and your sister-in-law about what he did. True story.

Depression

In the next stage, the parent realizes just how much work managing everything is, and also starts to worry that he’ll run out of money because returns are terrible. Which, when you move everything back to a full-service full-fee broker at a bank who sells you the bank’s own proprietary full-load mutual funds, they are. This took us about 6 months where I just had to hope that he wasn’t making truly catastrophic mistakes.

Acceptance

The parent realizes you had their best interests at heart and asks you gently if you’d be willing to look just once at their situation. You know, just to check it. Then they quickly give you the passwords back and accept your help in re-consolidating, simplifying and moving everything back to Fidelity. Tip: do not point that this what you tried to do in the first place.

In case I didn’t emphasize it before, for all you Sandwich Generation parents out there, get visibility as soon as you possibly can. This often is best accomplished in conjunction with a health scare of some kind as parents do not yield this information easily. Also, money is one of the great taboo subjects in our society, especially true between parents and children. This article from AgingCare.com lays out some interesting strategies; another one is from the Wall Street Journal.

Whatever you do, remember that it is not a one and done situation. It takes 4 stages. If you’re lucky.

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